Huixiang Nie , Linghui He , Anlin Zhao , Haijin Huang , Tao Wang , Jin Luo
{"title":"新的 8-癸硫基-10-甲硫基嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶衍生物的设计、合成和生物活性","authors":"Huixiang Nie , Linghui He , Anlin Zhao , Haijin Huang , Tao Wang , Jin Luo","doi":"10.1080/10426507.2023.2245528","DOIUrl":null,"url":null,"abstract":"<div><p>A series of new 8-decylthio-10-methylthio-pyrimido[5,4-<em>e</em>][1,2,4]triazolo[1,5-<em>c</em>]pyrimidine derivatives was prepared and characterized by FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The bioassay results revealed that the title compounds had moderate to excellent insecticidal activities against <em>Aphis fabae</em> at a concentration of 500 mg/L. Among them, 8-(decylthio)-2-((4-chlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (<strong>4l</strong>) exhibited the highest insecticidal activity, with 95% mortality. Moreover, 8-(decylthio)-2-((2,4-dichlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (<strong>4i</strong>) showed broad-spectrum postemergence herbicidal activities against <em>Abutilon theophrasti</em>, <em>Amaranthus spinosus</em>, <em>Chenopodium album</em>, <em>Digitaria sanguinalis</em>, <em>Echinochloa crusgalli</em>, and <em>Setaria viridis</em>, which were equivalent to the positive control flumetsulam. However, all new synthesized compounds displayed weak fungicidal activity against four kinds of phytopathogenic fungi including <em>Botrytis cinerea, phytophythora capsici, Elsinoe fewcetti,</em> and <em>Diaporthe medusaea</em>. Compound <strong>4l</strong> with remarkable insecticidal activity, and compound <strong>4i</strong> with excellent herbicidal activity could be promising lead compounds for further investigation.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, synthesis, and biological activity of new 8-decylthio-10-methylthio-pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives\",\"authors\":\"Huixiang Nie , Linghui He , Anlin Zhao , Haijin Huang , Tao Wang , Jin Luo\",\"doi\":\"10.1080/10426507.2023.2245528\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A series of new 8-decylthio-10-methylthio-pyrimido[5,4-<em>e</em>][1,2,4]triazolo[1,5-<em>c</em>]pyrimidine derivatives was prepared and characterized by FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The bioassay results revealed that the title compounds had moderate to excellent insecticidal activities against <em>Aphis fabae</em> at a concentration of 500 mg/L. Among them, 8-(decylthio)-2-((4-chlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (<strong>4l</strong>) exhibited the highest insecticidal activity, with 95% mortality. Moreover, 8-(decylthio)-2-((2,4-dichlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (<strong>4i</strong>) showed broad-spectrum postemergence herbicidal activities against <em>Abutilon theophrasti</em>, <em>Amaranthus spinosus</em>, <em>Chenopodium album</em>, <em>Digitaria sanguinalis</em>, <em>Echinochloa crusgalli</em>, and <em>Setaria viridis</em>, which were equivalent to the positive control flumetsulam. However, all new synthesized compounds displayed weak fungicidal activity against four kinds of phytopathogenic fungi including <em>Botrytis cinerea, phytophythora capsici, Elsinoe fewcetti,</em> and <em>Diaporthe medusaea</em>. Compound <strong>4l</strong> with remarkable insecticidal activity, and compound <strong>4i</strong> with excellent herbicidal activity could be promising lead compounds for further investigation.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-01-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723002253\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723002253","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Design, synthesis, and biological activity of new 8-decylthio-10-methylthio-pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives
A series of new 8-decylthio-10-methylthio-pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives was prepared and characterized by FTIR, 1H NMR, 13C NMR, and HRMS. The bioassay results revealed that the title compounds had moderate to excellent insecticidal activities against Aphis fabae at a concentration of 500 mg/L. Among them, 8-(decylthio)-2-((4-chlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (4l) exhibited the highest insecticidal activity, with 95% mortality. Moreover, 8-(decylthio)-2-((2,4-dichlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (4i) showed broad-spectrum postemergence herbicidal activities against Abutilon theophrasti, Amaranthus spinosus, Chenopodium album, Digitaria sanguinalis, Echinochloa crusgalli, and Setaria viridis, which were equivalent to the positive control flumetsulam. However, all new synthesized compounds displayed weak fungicidal activity against four kinds of phytopathogenic fungi including Botrytis cinerea, phytophythora capsici, Elsinoe fewcetti, and Diaporthe medusaea. Compound 4l with remarkable insecticidal activity, and compound 4i with excellent herbicidal activity could be promising lead compounds for further investigation.
期刊介绍:
Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.